


Coach Winchester

by DeansDirtyLittleSecret



Category: Supernatural
Genre: Explicit Language, Explicit Sexual Content, F/M, Implied underage reader, Reader-Insert, Smut, reader is not underage
Language: English
Status: Completed
Published: 2018-12-23
Updated: 2018-12-23
Packaged: 2019-09-25 02:07:09
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 5,105
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17112422
Author URL: https://archiveofourown.org/users/DeansDirtyLittleSecret/pseuds/DeansDirtyLittleSecret
Summary: Request: Imagine being a hunter and going undercover as a junior at a high school and coming across the Winchesters. Imagine Dean’s face when he finds out you aren’t really underage.  AND Imagine being one of the legal cheerleaders Dean talks about in Afterschool Special and fucking you as your gym teacher.





	1. Chapter 1

**Author's Note:**

> I decided to combine these two imagines together into one. I also changed the reader from a junior to a senior so it fit with the being legal concept. Set during episode 4.13 “After School Special.” I stuck pretty close to the storyline in the episode. I left the reader’s age vague so it could stay a reader insert.

You took a deep breath and straightened the red and white skirt so it hung evenly off of your hips. Who the hell decided that cheerleader’s skirts needed to be so damn short? It had to be a guy, no way it was a woman. You took a quick look at yourself in the full-length mirror on the back of the motel room door. You looked like a high school student, especially in the cheerleader outfit. Thank God you looked young for your age.

You’d been undercover at Truman High School for almost a week and you weren’t any closer to finding out what was killing off the students than you had been on your first day. The only thing you knew for sure was that it wasn’t a demon.

You grabbed your backpack off of the back of the chair, pulled the motel room door closed behind you and hurried the three blocks over to catch the school bus. Every day you had to spend in high school reminded you of why you were glad you were out. Fortunately, you’d managed to make a few “friends” after worming your way onto the cheer squad in less than two days.

You’d barely stepped off of the bus before one of those friends, Mandy, was glued to your side. She had her ready-to-gossip face on and you had to force yourself not to roll your eyes at the thought. This had to be the worst part of being undercover at a high school.

“OMG (Y/N),” Mandy squealed. “I have been trying to call you!”

You shrugged. You must have forgotten to turn on your cell phone after leaving the motel. “Sorry,” you muttered. “What’s up?”

She grabbed your arm and dragged you around the building to the doors leading to the gym. “Look,” she said, pointing through the tiny window in the door.

You looked through the door. “Holy shit,” you whispered. “Who is that?”

Through the gym door you could see a tall guy in red shorts, white knee socks and a white polo shirt with a red sweatband around his dark blond hair. You weren’t sure how it was possible, but he made that ensemble look good. Really good. He was gorgeous - tall, handsome, muscular and young. Why this guy was teaching high school instead of modeling or something like that was beyond you.

“That is Coach Roth,” Mandy explained. “He’s subbing for Ms. Boudreaux.”

“He’s our sub?” you breathed. “Whoa.”

“I know right,” Mandy giggled. “I’ve never looked forward to PE until today..”

You laughed with her and followed her into the building. You were actually looking forward to gym class yourself.

* * *

Life was so not fair. The past two days had been pure hell, stuck in PE with the most gorgeous guy in the world as your coach. A gorgeous guy who kept flirting with you and throwing out sexual innuendos like they were nothing. Most days you left class so hot and bothered that you had to take a cold shower before you could go to the next class. And Coach Roth had starred in his fair share of your nightly fantasies. Problem was, he thought you were a student, so there was no way he’d do anything more than flirt.  It was like torture. Any other time, you would have been all over him, flirting like crazy, trying to get him in your bed. As it was, you were spending a lot of time biting your tongue, holding back all of the flirty comments you were dying to say. You needed to wrap this case up and move on before you died of sexual frustration.

You’d just finished a rousing game of dodgeball, the only game Coach Roth apparently knew how to play, and you were headed for the locker room, your mind preoccupied with fantasies of what you’d like to do with the very beautiful PE teacher, when Mandy poked you in the arm.

“(Y/N), didn’t you hear him call you?” she said.

“What?” you mumbled. “Who?”

“Coach Roth,” she whispered, pointing at him.

You turned to see the substitute teacher standing on the other side of the gym with his arms crossed, staring at you. Today he was wearing a red sweatsuit and damn if he didn’t look good in that too. It emphasized his broad shoulders and his muscular thighs, clinging to his body in an almost obscene manner. You wished you could see what was underneath the sweatsuit. You pushed those thoughts out of your mind and hurried across the gym.

“You wanted to see me, Coach Roth?” you said, stopping in front of him.

“Miss (Y/L/N), you’re a senior, right?” he asked. “About to graduate?”

“Yes sir. I’m eighteen,” you added helpfully. You forced yourself not to stare at his full, pink lips, though his sparkling green eyes weren’t any better. You were actually much older than that, but you couldn’t tell him that. But it didn’t hurt to point out the fact that you were of legal age.

“Well, you know, I’m only here until Ms. B gets back from Massachusetts, so I was wondering if…..” He was interrupted by the new school janitor poking his head into the gym door and catching his eye. He gestured wildly at him.

Coach Roth sighed heavily, glaring at the man at the door. He waved him off and then turned back to you.

“Look, could you come to my office after school?” he asked. “Just for a few minutes? I have something I’d like to ask you.”

Confused, you nodded your head. “Sure,” you replied. “I can do that.”

The sound of a throat clearing carried across the empty gymnasium. Coach Roth rolled his eyes and yelled “Just a minute,” before turning back to you.

“I’ll see you then,” he smiled before hurrying across the gym.

You turned to head back to the locker room, but you caught a snippet of conversation between the two men as the door was swinging shut and you could have sworn you heard the words vengeful spirit. Curious as to what they were talking about, you sidled quietly up to the door, pushing it open just a couple of inches until you could hear what they were saying.

“Hey, you hear what happened in the home ec class?” the janitor asked.

“Oh, Sam, you’d be surprised what you hear about in here,” Coach Roth laughed. “So the kid had ectoplasm leaking out his ear?”

“Which only comes from a seriously pissed off spirit,” the guy Roth had called Sam said. “It’s got to be ghost possession.”

Surprised, you missed the next part of their conversation as you tried to figure out who the hell these guys were. They had to be hunters, obviously here for the same reason you were. A grin spread across your face as you realized what that meant.

Your attention was drawn back to the two men in the hallway when you heard Coach Roth telling the other guy that he’d better go.

His hand was on the door, ready to pull it open and most likely catch you hiding behind it, when Sam stopped him.

“Dean, stay away from the cheerleaders,” he ordered.

So Coach Roth’s name was Dean, huh? You ducked around the side of the bleachers as the door came all the way open, not quite ready for him to see you. Once he crossed the gym and went into his office, you hurried to the locker room to change.

You were sure you knew who these guys were. You didn’t hunt as long as you had without hearing their names come up pretty often. They were practically legendary. Sam and Dean Winchester.

You spent the rest of the day trying to figure out who the vengeful spirit might be, questioning students and faculty alike. It wasn’t always easy, especially when you were wearing a cheerleader uniform. Sometimes, they just didn’t take you seriously, but you did manage to gather some information, though a lot of it was gossip. At this point, you’d take what you could get.

When the final bell of the day rang, you hurried to the gym and your appointed meeting time with Coach Roth, aka Dean Winchester. You were going to take full advantage of the fact that you knew he wasn’t a teacher. And maybe you’d make him pay for all the flirting.

You knocked lightly on the office door. You couldn’t see inside because all of the blinds were closed, but you heard the faint “come in” from the other side of the door, so you opened it and entered the office. You closed the door behind yourself.

“(Y/N,)” Dean said. “Thank you for coming down here.”

“I was really glad you asked to see me, Coach Roth,” you said.

“Really?” he said as he came out from behind the desk to lean against the front of it. “Why is that?”

You dropped your backpack to the floor as you walked toward him. You put on your best innocent look, a small smile on your face. “I’ve been wanting to tell you how glad I am that you are subbing for Ms. B. In fact, I wish you could be our teacher for the rest of the year.” You stopped just inches from Dean. “I’d really like that.”

Dean swallowed noticeably. “Y…you would?” he stuttered. He shifted uncomfortably on the edge of the desk.

“Oh, definitely,” you murmured as you took another step forward, planting yourself right between his legs. You put your hands on his thighs, leaned forward and brushed a kiss across his lips. “I want a chance to feel these lips sucking on every inch of my body.” You ran your hands up his thighs until you reached the growing bulge under his light sweatpants. You rubbed him slowly up and down through the fabric, feeling his cock grow hard under your hand. “I want to feel this inside me, filling me up.”

“(Y/N), what do you think you’re doing?” he groaned through his clenched teeth. He grabbed your hands and pushed them away. “I’m your teacher….”

“But Coach Roth,” you whimpered. “Or should I say Coach Winchester?”

Dean stood up so suddenly that you stumbled backward. “What did you say?”

You crossed your arms and stared at him. “You’re Dean Winchester,” you said. “And the janitor, that’s your brother Sam.”

“How the hell do you know that?” he demanded.

You hurriedly explained who you were, why you were there and how you knew them. You weren’t sure he believed you until you told him to call Bobby Singer and he would vouch for you. He’d seemed unsure at first, but once you pulled out Bobby’s name, he seemed to believe you.

He nodded at you. “So you’re here….”

“For the same reason you are,” you finished. “I’m trying to figure out what is killing these kids.”

“Any luck?” he asked.

You shook your head. “Not really,” you said. “Just a lot of speculation. You?”

“Some. Sam has an idea who it is. Or who the spirit is, I guess.”  He stared at you for a couple of seconds, until you started to feel uncomfortable. “So, how old are you?” he finally asked, his eyebrow quirked slightly as he returned to leaning against the desk.

You moved back between his legs, returning your hands to his thighs. “I’m older than eighteen, that’s for damn sure” you whispered. “Completely legal.”

Dean’s smile widened. He rested his hands lightly on your hips. “I think you were telling me what you wanted me to do to you,” he growled.

“All I’ve been able to think about all week is what I want you to do to me,” you purred. You took his hands and pulled them around you until they were resting on your ass. He pulled you tight against him; you could feel his erection growing again. He kneaded the soft skin under his hands and finally captured your lips in his. You sighed as his tongue slid into your mouth. He tasted like heaven.

Dean’s hands slid further under your skirt until his thumbs were hooked in your red panties and he was yanking them down, hurriedly pushing them down your thighs. His hand dipped between your legs and then his long fingers were inside you, pumping rapidly. You squirmed and pushed yourself against his hand, encouraging him. You shoved your hands down the front of his sweatpants and took his cock in your hands, running your hand up and down his substantial length.

“God, I love you in this skirt,” he groaned, as his hips bucked in your hand. He bit at your neck as he put his hand under your sweater and grasped your breast, thumbing the already erect nipple through the lacy fabric of your bra. “So sexy,” he murmured. “So naughty.”

“Mmm,” you hummed. You stepped away from him, reluctantly breaking contact.

“Where are you going?” he mumbled.

You grabbed the bottom of your sweater and pulled it over your head, tossing it to the floor at your feet. You dropped to your knees in front of Dean, grabbed the waistband of his pants and pulled them down until his cock was free. You took the base in your hand, leaning forward until you could wrap your lips around it. You gently licked and swirled your tongue across the tip, tasting the pre-come leaking from it.

“Oh God, (Y/N),” he moaned.

You looked up at Dean through your lashes. You watched him as you slid him into your mouth as far as possible, until he was bumping the back of your throat. You slowly slid him out of your mouth, tasting every inch of him as you did.

“I want you to fuck my mouth, Coach Winchester,” you murmured before sliding your lips over his cock again.

“Shit,” Dean groaned and then he was moving, his hands in your hair, his hips thrusting repeatedly into the warm heat of your mouth as you swallowed him down. Desire pooled in your stomach as you sucked Dean into your mouth, your hips jerking against nothing, desperate for something to ease your aching core.

Dean must have known what you needed, because he grabbed your arm and pulled you to your feet. He turned you around so you were leaning over the desk, then you felt his warm hands pulling your underwear the rest of the way off. His lips kissed a trail up the back of your legs, his tongue briefly diving into your dripping wet pussy before moving up your ass. He nibbled at your ass, his fingers dancing over you until you were panting and begging.

“Dean, please,” you gasped.

His hands gripped your hips hard as he leaned over you. You could feel his hard cock pressing against your ass and you wiggled against him. “What did you call me?” he snarled.

“I’m sorry,” you breathed. “Coach Winchester, please, please don’t tease me.”

“Tell me what you want me to do to you, (Y/N),” he ordered.

You were so turned on, so desperate to feel him inside you, that you could barely talk. You squirmed again. “I…I want you to fuck me,” you finally moaned.

“What do you say?” Dean growled in your ear.

“Please Coach Winchester, fuck me,” you begged. “Fuck me now!”

You felt the tip of Dean’s cock rubbing against your entrance and then he was sliding into you, stretching you wide. He moved slowly, pumping gently as he gave you time to adjust to his considerable size. He put a hand on your shoulder and held you in place as he thrust into you. Once you had taken him completely, he really began to move, slamming into you hard, every movement hitting your sweet spot. He pulled you up, his hand slipping down your stomach until he was thumbing your clit. You groaned as Dean rubbed your clit and his thrusts hit the perfect spot just right and then your were coming, moisture running down your thighs as Dean pounded into you relentlessly. The orgasm seemed to go on forever, draining you of every ounce of energy.

A few seconds later, Dean slammed into you one last time, bottoming out as his cock twitched inside you, his breath heavy on your neck, his arms tight around you as he came.

You leaned over the desk on your elbows, trying to catch your breath. Dean’s lips grazed over your shoulders and neck, kissing and nibbling the bare skin.

“Well, Coach Winchester,” you said, “how’d I do?”

He turned you around and kissed you until you were breathless. “You get an A, Ms. Y/L/N” he chuckled. “Maybe even an A+.” His lips returned to yours and you lost yourself in the overwhelming force that was Dean Winchester.


	2. Chapter 2

You relaxed into the worn vinyl seat, attempting to hide yourself in the corner of the dimly lit bar. You needed a drink and soon. This last hunt had been a bitch, wearing you out. You’d decided to take a few days off to recuperate. Day two found you seeking solace in the nearest bar. That or something to do. You were actually starting to get bored.

The waitress finally made her way to your table. She took one look at you and rolled her eyes.

“Can I see some ID please?” she said.

Prepared, you pushed your license across the table. She picked it up and examined it closely. When she finally handed it back to you, it was with a wary smile.

“Sorry,” she muttered. “You look really young.”

You returned her smile. “I get that a lot. Can I get a beer?”

“Sure,” she replied. “I’ll be right back.”

Once you had your beer, you turned so you could check out the other patrons in the bar. Maybe someone would catch your eye. Of course, that was a big maybe. No one had caught your eye since Dean Winchester had rolled into your life like a gale force storm and quite literally swept you off your feet. He pretty much consumed your every waking thought. No one would have ever guessed that the two of you had spent less than 24 hours together, considering how much you thought about him. Of course, it was hard to forget a guy like Dean.

You sighed, frustrated. It had been more than three months since you’d run into Dean and his brother at Truman High School, all three of you undercover, trying to figure out what was killing students. After you and Dean had figured out that you weren’t student and teacher, the two of you had had one of the most amazing sexual encounters you’d ever experienced, right in the gym teacher’s office, with you still in your cheerleader’s outfit. The memory of that encounter still made you hum with desire. Unfortunately, once the vengeful spirit was taken care, you and Dean had gone your separate ways and you hadn’t seen him since.

You sipped at your beer, eyeing the rapidly growing crowd. Maybe it was time to go, before the drunk assholes came out of the woodwork and started hitting on you.

“Well, look who we have here,” you heard from behind you.

“Too late,” you said to yourself, your back stiffening immediately. You turned around, ready to shoot down whoever had targeted you as a potential pick-up.

Instead, your mouth dropped open when you saw the tall, muscular, green-eyed hunter you’d just been thinking about. He was leaning against the edge of the booth, hip cocked, a beer in his hand, a smirk on his gorgeous full lips.

“Dean,” you breathed. “What are you doing here?”

“Sammy and I just finished up a hunt a couple of towns over,” he told you. “We were headed out, but I needed a beer. Or two or three.” He pointed at the seat next to you and you nodded. He slid into the booth, his leg pressed against yours, his arm over the back of the seat, his fingers just barely brushing your shoulder. “So, we stopped here. And I found you. Lucky me.” He leaned so close to you that you could smell the beer and mint gum on his breath. You shivered.

“So you did,” you murmured. You looked behind him. “Where’s your brother?”

Dean shrugged. “Who cares?” He took a long drink of his beer. “So what are you doing?”

“Taking a few days off,” you answered. “Trying to relax.”

“I could help you relax,” he whispered, his lips just inches from yours.

“Oh really, Coach Winchester,” you murmured, kissing him lightly on the lips, your hand sliding up his thigh.

Dean groaned, low in the back of his throat so only you could hear him. “You’re such a tease, Miss (Y/L/N).” He cupped the back of your head and pulled you to him, licking across your lips, his tongue pushing into your mouth.

You grabbed the front of his button down shirt, pulling him as close to you as you could get in the small booth. You moved your hand higher up Dean’s leg, until it was resting on the erection you could feel growing under your hand. You traced a finger along the waistband of his jeans as you returned his kisses.

“I think we should get out of here,” you whispered.

“Whose motel?” he asked, breathless.

“Mine,” you replied, pushing him out of the booth. “No interruptions from brothers.”

Dean chuckled as he took your hand and helped you up. He let you lead him from the bar and around the corner to the motel you were staying at. You bypassed the front desk, instead using a door around the back you had discovered your first night there. Dean couldn’t keep his hands or his mouth off of you, he touched and kissed you every step of the way. He stood behind you as you unlocked the motel room door, his arms around your waist and his lips moving over every available inch of your neck.

“God, (Y/N), the only thing that would make this better would be if you were in that cheerleader’s outfit,” he purred in your ear.

You finally unlocked the door and pushed it open. You turned around and put your arms around Dean’s neck, tugging him with you into the room.

“Oh, yeah,” you murmured. “Well, I really liked those little red shorts you had. Too bad you don’t have those around.”

“Maybe I still have them,” he laughed.

Dean pulled at your clothes, but you pushed him away. He groaned and tried to grab you, but you danced backwards, headed for the bathroom.

“Relax, Coach Winchester, you need to wait just a little longer,” you giggled. “I’ll be right back.” You slammed the bathroom door, laughing at Dean’s confused face. You yanked your suitcase out from underneath the counter, hurriedly digging through it. Buried at the bottom, under several pairs of jeans and an old Led Zeppelin shirt was the cheerleader uniform. You shook it out and stripped out of your jeans, t-shirt and undergarments, dropping them into the suitcase. You stepped into the skirt, pulling it around your waist. When you turned around, you could see just a hint of your naked ass below the edge of the skirt. Instead of the long-sleeved sweater that accompanied the uniform, you pulled on a Truman High School tank top, your naked breasts pushing against the thin material. You shot yourself an appraising look before yanking open the door and stepping out of the bathroom.

Dean was sitting on the end of the bed; he’d kicked off his shoes and stripped down to nothing but his boxer briefs. He took a deep breath when you came out of the bathroom, his eyes wide.

“I’ll be damned,” he breathed.

“Oh not yet, Coach Winchester,” you purred. “But you will be.”

You crossed the room until you were standing in front of Dean. He put his hands on your hips as you straddled him and took his head in your hands, tilting his head back so you could kiss him.

You were both panting when you broke off the kiss. Dean dropped his head and nudged the edge of your tank top up with his nose. He mouthed the sensitive skin of your stomach, as he moved his hands down your body until he was grasping the bare skin of your bottom. He kept a hold of you as he laid back on the bed, his thumbs rubbing up and down your hip bones as he moved you with him. He pulled you up his body until you were sitting on his chest, your knees on either side of his head. He ran his hands up and down your thighs, staring into your eyes, a little smirk on his face and then his hands tightened on your ass and then he was yanking you toward him, his tongue skating up the inside of your thigh.

Dean flipped up the skirt, pulled you to him and buried his face between your thighs with a deep growl. His tongue flicked against your clit lightly before he sucked it into his mouth, rolling the nub with his tongue. The skirt fell over his face and you could no longer see what he was doing. But you could  _feel_  everything.

The flat of his tongue slowly slid along your folds, stabbing teasingly into your entrance before retreating to continue its exploration of you. You whined, your hips rolling forward, silently begging for more. His hands kneaded your bottom, pulling you closer and closer, until his mouth was tight against your mound and his tongue was deep inside you. He pulled your hips slightly forward as his tongue moved and his mouth sucked, and you were lost, your head rolling back on your neck and your mouth falling open as a low moan slipped past your lips. You held his forearms as he rocked your body back and forth, helping you to ride his tongue, letting him fuck you with his mouth until you were so overcome by the feelings roaring through you that you were screaming Dean’s name, the climax building and building until you were breathless and spent. But Dean wouldn’t let up, he continued devouring you, his mouth and tongue taking you to heights you’d never hit before.

When it seemed Dean had finally had his fill of you, he slid you down his body, kissing your now sensitive thighs as you moved. Once your cheerleader skirt slipped off of his face, you could see the self-satisfied smirk he wore like a badge of honor. He rolled you to his side and caught your lips in an intoxicating kiss as he slid his hand under your tank top and pinched the already erect nipple between his thumb and forefinger, twisting and tugging at it until you were arching your back and panting, pushing your breast into his hand. He put his fingers under your skirt, and let them dance over you slowly, just before he carefully slipped his middle finger inside you, a second finger joining it almost immediately.

“Touch me, (Y/N),” he ordered as his fingers moved inside of you.

You couldn’t obey fast enough. You slipped your hand into his boxers until you were able to grasp his cock and then you were gliding your hand up and down his length, feeling him grow harder with every movement. Dean’s fingers moved in concert with the movements of your hand and you could feel yourself getting close again, balanced right on the edge.

You whimpered uncontrollably when Dean was suddenly gone, his hands no longer on your body and his lips no longer kissing yours. “Dean,” you groaned, frustrated at the loss of him pleasuring you. You looked up to see him leaning over you.

“What did you call me, (Y/N)?” he snarled.  “I think you meant….”

“Coach Winchester,” you finished. “I meant Coach Winchester.”

Dean smiled as he settled himself at the top of the bed, his back against the headboard, completely naked. He crooked a finger at you, gesturing for him to come to you. You turned and crawled up the bed until you were kneeling between his legs.

“You don’t need this anymore,” he said, pulling your tank top over your head. He took your face in his hands, his emerald green eyes staring into your (y/e/c) ones. “I want you to fuck me,” he demanded. “I want you to ride my cock, hard.  Do you understand me, Miss (Y/L/N)?”

You nodded, heat blasting through you as you straddled him. He kept one hand on your waist as he guided himself to your entrance and pulled you down onto him, until he was totally encompassed by your wet heat.

“Fuck yes,” he groaned. “Now move.”

You nodded and carefully moved your hips forward, then back, experimenting with the position. You opened your legs wider and Dean shoved his hips up, slamming into you just right, hitting your sweet spot perfectly. You moaned and starting moving, riding Dean hard and fast. He dropped his head and took your breast in his mouth, sucking at the nipple. Every thrust of his hips hit your g-spot perfectly, sending waves of pleasure rolling through you. You gripped his shoulders and moved faster, taking him as deep as possible, wanting to feel every inch of him inside you.

“Oh, God, yes,” you moaned as Dean pumped into you, his hips pistoning madly and then you were coming again, the second orgasm impossibly better than the first.

With a loud grunt, Dean followed right behind you, holding you tight against him as he spilled his seed inside you. He kissed you, hard and demanding at first, but then changing to soft and sweet as he hugged you to his chest.

You were a mess, barely able to move, draped over Dean. He laughed as he rolled you to your side and cuddled up next to you.

“That was amazing,” he mumbled, nibbling the soft spot just under your ear.

“So I get another A?” you breathed.

“Hmm, maybe,” he said. “There might be a couple more tests you have to pass first.” His fingers danced down your spine as he spoke until he reached your bottom. He cupped it with both hands and pulled you against him.  “You okay with that, Miss (Y/L/N)?”

“Whatever you say, Coach Winchester,” you whispered. “Whatever you say.”


End file.
